EP0708798B1 - Suspension for use in electrophoretic image display systems - Google Patents
Suspension for use in electrophoretic image display systems Download PDFInfo
- Publication number
- EP0708798B1 EP0708798B1 EP94920792A EP94920792A EP0708798B1 EP 0708798 B1 EP0708798 B1 EP 0708798B1 EP 94920792 A EP94920792 A EP 94920792A EP 94920792 A EP94920792 A EP 94920792A EP 0708798 B1 EP0708798 B1 EP 0708798B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- particles
- pigment particles
- pigment
- suspension medium
- charge control
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000725 suspension Substances 0.000 title claims description 62
- 239000002245 particle Substances 0.000 claims description 92
- 239000000049 pigment Substances 0.000 claims description 72
- 239000003795 chemical substances by application Substances 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 17
- 230000002378 acidificating effect Effects 0.000 claims description 14
- 230000005484 gravity Effects 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 9
- 239000000992 solvent dye Substances 0.000 claims description 7
- 238000004873 anchoring Methods 0.000 claims description 6
- 239000000523 sample Substances 0.000 claims description 6
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims description 5
- 229920002367 Polyisobutene Polymers 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- 229950011008 tetrachloroethylene Drugs 0.000 claims description 5
- 238000000498 ball milling Methods 0.000 claims description 3
- 230000004888 barrier function Effects 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000012860 organic pigment Substances 0.000 claims 3
- 239000002904 solvent Substances 0.000 description 11
- 239000011324 bead Substances 0.000 description 9
- 239000000975 dye Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 8
- 239000012530 fluid Substances 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 230000003993 interaction Effects 0.000 description 5
- 238000003801 milling Methods 0.000 description 5
- 239000001052 yellow pigment Substances 0.000 description 5
- OCQDPIXQTSYZJL-UHFFFAOYSA-N 1,4-bis(butylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(NCCCC)=CC=C2NCCCC OCQDPIXQTSYZJL-UHFFFAOYSA-N 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 230000006641 stabilisation Effects 0.000 description 4
- 238000011105 stabilization Methods 0.000 description 4
- 239000004408 titanium dioxide Substances 0.000 description 4
- IAFBRPFISOTXSO-UHFFFAOYSA-N 2-[[2-chloro-4-[3-chloro-4-[[1-(2,4-dimethylanilino)-1,3-dioxobutan-2-yl]diazenyl]phenyl]phenyl]diazenyl]-n-(2,4-dimethylphenyl)-3-oxobutanamide Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)C(C(=O)C)N=NC(C(=C1)Cl)=CC=C1C(C=C1Cl)=CC=C1N=NC(C(C)=O)C(=O)NC1=CC=C(C)C=C1C IAFBRPFISOTXSO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
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- 238000005189 flocculation Methods 0.000 description 3
- 230000016615 flocculation Effects 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000007600 charging Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 0 *CC(CC(N1*)=O)C1=O Chemical compound *CC(CC(N1*)=O)C1=O 0.000 description 1
- LQZFGPJGXVFSTR-UHFFFAOYSA-N 2-[[2-chloro-4-[3-chloro-4-[[1-(2-methylanilino)-1,3-dioxobutan-2-yl]diazenyl]phenyl]phenyl]diazenyl]-n-(2-methylphenyl)-3-oxobutanamide Chemical compound C=1C=CC=C(C)C=1NC(=O)C(C(=O)C)N=NC(C(=C1)Cl)=CC=C1C(C=C1Cl)=CC=C1N=NC(C(C)=O)C(=O)NC1=CC=CC=C1C LQZFGPJGXVFSTR-UHFFFAOYSA-N 0.000 description 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- 241001561902 Chaetodon citrinellus Species 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 108010092377 aminoalcoholphosphotransferase Proteins 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000007786 electrostatic charging Methods 0.000 description 1
- 238000004924 electrostatic deposition Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 239000013047 polymeric layer Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000002352 surface water Substances 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Images
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/165—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on translational movement of particles in a fluid under the influence of an applied field
- G02F1/166—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on translational movement of particles in a fluid under the influence of an applied field characterised by the electro-optical or magneto-optical effect
- G02F1/167—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on translational movement of particles in a fluid under the influence of an applied field characterised by the electro-optical or magneto-optical effect by electrophoresis
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G17/00—Electrographic processes using patterns other than charge patterns, e.g. an electric conductivity pattern; Processes involving a migration, e.g. photoelectrophoresis, photoelectrosolography; Processes involving a selective transfer, e.g. electrophoto-adhesive processes; Apparatus essentially involving a single such process
- G03G17/04—Electrographic processes using patterns other than charge patterns, e.g. an electric conductivity pattern; Processes involving a migration, e.g. photoelectrophoresis, photoelectrosolography; Processes involving a selective transfer, e.g. electrophoto-adhesive processes; Apparatus essentially involving a single such process using photoelectrophoresis
Description
JAR HEIGHT | JAR DIAMETER | BEAD CHARGE | SUSPENSION SAMPLE SITE |
48mm | 61mm | 200g | 50g |
68mm | 81mm | 400g | 100g |
113mm | 81mm | 800g | 200g |
Claims (14)
- An electrophoretic display composition comprising:a suspension medium comprising tetrachloroethylene and sec-butyl benzene;charged pigment particles suspended in said suspension medium, 50 wt. % of said pigment particles having been formed by a coupling reaction in the presence of at least one surface active agent, said suspension medium having a specific gravity corresponding to that of said pigment particles, said pigment particles defining surfaces having at least one acidic hydrogen site per molecule and said pigment particles being selected from the group consisting of Pigment Yellow 14 and Pigment Yellow 55;a solvent dye dissolved in said suspension medium; anda charge control agent, said charge control agent being adsorbed on said pigment particles and having a basic anchoring group for reacting with said pigment particles to form charge pairs therewith and having a polymer chain extending therefrom, thereby providing a steric barrier between particles.
- A composition according to claim 1, wherein the specific gravity of said suspension medium is 1.43 g/ml.
- A composition according to claim 2, wherein said suspension medium is present in a concentration of 98.7% by weight.
- A composition according to claim 4, wherein said solvent dye is present in a concentration of 0.12% by weight.
- A composition according to claim 1, wherein the pigment particles are Pigment Yellow 14.
- A composition according to claim 6, wherein said pigment particles are present in said composition in a concentration of 0.8% by weight.
- A composition according to claim 8, wherein said charge control agent is present in a concentration of 0.4% by weight.
- A process for forming an electrophoretic display composition comprising the steps of:forming a first plurality of discrete organic pigment particles by a coupling reaction in the presence of at least one surface active agent, each of said first plurality of pigment particles defining a surface ;providing a second plurality of said discrete organic pigment particles which has not been treated with a surfactant, each of said second plurality of pigment particles defining a surface;dispersing said first and second plurality of discrete organic pigment particles in a weight ratio of 50:50 in a suspension medium of tetrachloroethylene, each surface having at least one acidic hydrogen site and said first and second plurality of particles being selected from the group consisting of Pigment Yellow 14 and Pigment Yellow 55;providing a charge control agent having at least one basic anchoring group in said suspension medium;adsorbing said charge control agent on the surfaces of said first and second plurality of particles and reacting said acidic hydrogen sites with said basic anchoring groups, thereby forming charge pairs and polymer chains extending from each surface to provide a steric barrier between the particles of both said first and second plurality of particles;dissolving a solvent dye in said suspension medium; andadding an effective amount of secondary-butyl benzene to said medium to obtain a specific gravity of said suspension medium which is the same as that of said first and second plurality of pigment particles.
- The process according to claim 10, wherein said adsorbing step comprises ball milling said first and second plurality of pigment particles and said charge control agent together for at least two hours.
- The process according to claim 10, wherein said dissolving step is performed prior to said adsorbing step and wherein said adsorbing step comprises ballmilling said first and second plurality of pigment particles and said charge control agent together for at least eight hours.
- The process according to claim 10, further including the step of exposing said suspension medium to an ultrasonic probe to drive out any dissolved gasses.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/092,749 US5380362A (en) | 1993-07-16 | 1993-07-16 | Suspension for use in electrophoretic image display systems |
US92749 | 1993-07-16 | ||
PCT/US1994/007042 WO1995002636A1 (en) | 1993-07-16 | 1994-06-21 | Suspension for use in electrophoretic image display systems |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0708798A1 EP0708798A1 (en) | 1996-05-01 |
EP0708798A4 EP0708798A4 (en) | 1997-12-10 |
EP0708798B1 true EP0708798B1 (en) | 2000-04-26 |
Family
ID=22234941
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP94920792A Expired - Lifetime EP0708798B1 (en) | 1993-07-16 | 1994-06-21 | Suspension for use in electrophoretic image display systems |
Country Status (6)
Country | Link |
---|---|
US (1) | US5380362A (en) |
EP (1) | EP0708798B1 (en) |
JP (1) | JPH09500458A (en) |
CA (1) | CA2165068A1 (en) |
DE (1) | DE69424170T2 (en) |
WO (1) | WO1995002636A1 (en) |
Cited By (5)
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US6392785B1 (en) | 1997-08-28 | 2002-05-21 | E Ink Corporation | Non-spherical cavity electrophoretic displays and materials for making the same |
US6473072B1 (en) | 1998-05-12 | 2002-10-29 | E Ink Corporation | Microencapsulated electrophoretic electrostatically-addressed media for drawing device applications |
US6693620B1 (en) | 1999-05-03 | 2004-02-17 | E Ink Corporation | Threshold addressing of electrophoretic displays |
US6704133B2 (en) | 1998-03-18 | 2004-03-09 | E-Ink Corporation | Electro-optic display overlays and systems for addressing such displays |
US8466852B2 (en) | 1998-04-10 | 2013-06-18 | E Ink Corporation | Full color reflective display with multichromatic sub-pixels |
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US6120588A (en) * | 1996-07-19 | 2000-09-19 | E Ink Corporation | Electronically addressable microencapsulated ink and display thereof |
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US6727881B1 (en) | 1995-07-20 | 2004-04-27 | E Ink Corporation | Encapsulated electrophoretic displays and methods and materials for making the same |
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- 1994-06-21 JP JP7504567A patent/JPH09500458A/en active Pending
- 1994-06-21 CA CA002165068A patent/CA2165068A1/en not_active Abandoned
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Also Published As
Publication number | Publication date |
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DE69424170D1 (en) | 2000-05-31 |
DE69424170T2 (en) | 2000-12-21 |
WO1995002636A1 (en) | 1995-01-26 |
EP0708798A4 (en) | 1997-12-10 |
CA2165068A1 (en) | 1995-01-26 |
US5380362A (en) | 1995-01-10 |
JPH09500458A (en) | 1997-01-14 |
EP0708798A1 (en) | 1996-05-01 |
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